20 Ways to Win Your 20s

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I’m very, very picky about the caliber of man I take seriously as a mate—as opposed to those I’ll make a 4 AM booty call. I’m almost Seinfeldian in my standards (hence why I’ve been single4eva), but a decade of dating has taught me that all of the good men in their 30s–the “keepers”–made good choices in their 20s.

There are plenty of other lists that will tell you to “start saving” and “let go of the need for approval.” Don’t get me wrong. Those things are important, but women don’t care how much you have in your 401K if you can’t change a tire or follow through on a plan. If you want to be all the man you can be in your 30s, here are 20 ways to win your 20s.

DON’T BE AFRAD TO FAIL
If you are a male who made it through your teens and didn’t die doing something dangerously reckless while your testosterone levels were surging, consider yourself lucky. Now it’s time to start taking some calculated risks. That’s why we have our 20s–to fuck up. By the time I was 27 I had already been in rehab, divorced and gone bankrupt. Now I’m not suggesting you start doing drugs, marry a Russian and fund your own start-up (in that order), but I am glad I banged them all out in my 20s because rehab, divorce and bankruptcy in your 40s and 50s are a shit show. The younger you are, the easier it is to bounce back from physical injuries, heartbreak, hardship and hangovers. Fact.

BECOME A CRITICAL THINKER
How do you do this? By pushing yourself outside of your bubble. I realize it’s increasingly harder to do in the ultra-personalized world where your tribes and various algorithms are constantly flattering you and reinforcing your biases, but seek people and information that don’t only confirm your limited point of view. Challenge yourself to see things from ALL sides, not just YOUR side. If you only read liberal, read some conservative, and vice-versa. Perspective is everything. Try to make yours a bird’s-eye-view.

TRAVEL
One of the best ways–if not THE best way–to expand your worldview is travel. And I don’t mean a ski trip with your friends (although that definitely has its place). I mean a backpack and a Lonely Planet guide. If you don’t need some type of shot and a passport for where you’re going, you’re not traveling. You’re vacationing. Push yourself to see different countries alone. If funds are limited, no matter where you live, there is always plenty to do and see in your own backyard. If I’ve learned anything from extensive stays in national parks all over the world, it’s that foreigners usually make much better use of them than the citizens of that country. Put those parks and those passports to use.

EXPERIENCE IS KING
Make a list of everything that scares you, from doing stand-up comedy to bungee-jumping, and conquer it. I don’t believe in “bucket lists.” I believe in “fuck it lists.“ Like, “Fuck it. Why not go to New Zealand and learn how to horseback ride?” You only live once. If you live your 20s like you’re dying, when the grown-up responsibilities set in and you have kids and mortgages and a company to run, it all isn’t going to feel like a death sentence. Have no regrets.

WORK TOWARDS MAKING A NICE HOME
That being said–do your best to get the mattress off the ground. You can get away with the box spring on the floor in your early 20s (I had a blow-up mattress and shelves made of cardboard boxes at one point), but when you’re pushing 30 and you still don’t have a bed frame, it’s not a good look. I’m always impressed when I go to a guy’s place and you can tell he takes pride in his home. Properly hung pictures on the wall? Panty-droppers. IKEA IS YOUR FRIEND.

WORK A MANUAL LABOR JOB
Manual labor teaches you the value of hard work and, not to sound like your grandpa or anything, if you know what it feels like to break your back in the sun or stand on your feet all day, then you know how a huge portion of the world makes a living. People who have worked at least one manual labor job—or volunteered doing hard manual labor work–are just nicer. I’m sorry paper-pushers who have never washed a dish or lifted anything heavy in your life —you are usually the least patient, least empathetic individuals on the planet and, speaking for wait staff everywhere, we hate you.

LEARN HOW TO DO SHIT
Particularly, cook more than eggs and pasta. Playboy has been killing it with all the cooking coverage, so you have no excuse. Also a panty-dropper—a man who can cook me a meal and change a tire. Learn some basics: How to build a fire. Patch some drywall. Take a welding class. Grow some food. Most cities have super-cool classes at local fire stations that teach you how to be a good first responder in a crisis. I like my men the way I like my basements: sturdy and prepared for the apocalypse.

THESE ARE YOUR ‘EXPERIMENTAL YEARS’
Enjoy them. Have a threesome. Try out some butt stuff—with her or you. I don’t know what you’re into. Maybe you don’t even know what you’re into. This is the time to try it all out. I’m not advocating drugs and binge-drinking, but the best time to do it is your 20s. Being a fall-down drunk or a cokehead after 30 is just sad. Thirty is when you start drinking responsibly or quit drinking. You get a free pass in your 20s to say, “Oh, those were my 20s.” Use it. Oh, and use Uber. Drinking and driving is for morons, especially with the advent of ride sharing. A DUI is a mistake you want to avoid no matter what the decade.

GET SOME NEW HOBBIES
Stop spending so much of your time playing video games. I’m not saying stop altogether. Just allocate more time to something else. Anything you start today you will do amazingly in five years. The time is going to pass anyway. So if you’ve always wanted to play the guitar or learn Mandarin or play golf, your 20s are the time to master things that are impressive to master.

CHASE YOUR PASSIONS
After 21 you get the Fast Trak Pass to the grave. You blink, and you’re 35. If you aren’t sure what you’re passionate about, use your 20s to find out. Try different jobs. Volunteer. Protest. Save the whales. Save the krill from the whales. Leave a boring job you took because it impressed your parents. Your parents are going to die, and you’re going to be stuck in a job you hate. Passion for what you do is what will sustain you. Passion is the pilot. The work is the fuel.

FORGIVE YOUR PARENTS
Most of them did the best they could. Maybe they didn’t. Either way, the sooner you realize that blaming society and your parents and everyone and every fucking other thing is a pointless, childish waste of time, the better for everyone. A victim mentality isn’t attractive. Get some therapy, get over it and get on with it.

TALK TO YOUR GRANDPARENTS
If they’re still alive, and you have the opportunity, talk to your grandparents. My cousins sat down and recorded my grandfather recalling his experience during WWII, and it’s remarkable what he endured and experienced. You can learn from their wisdom, and trust me THEY’VE SEEN SOME SHIT.

BE OKAY WITH BEING VULNERABLE
Men are put under a lot of pressure to be tough. You don’t have to cry during puppy rescue commercials, but cultivating a bit of sensitivity and letting your guard down won’t kill you. It will only make you stronger. Don’t be afraid to open your heart. I know the Tinder hellscape makes it super hard with everyone flaking and ghosting and disappearing like it’s The Matrix, but take a chance on love. It’s exhilarating.

EXPERIENCE MANY WOMEN
I don’t mean run around sticking your dick in everything you can, although your 20s are absolutely the best time for this kind of behavior. I mean experience many different types of women. Your early 20s are like that moment at Coldstone Creamery when you’re sampling every flavor before you have to buckle down and make some difficult ice cream choices. This is the best way to know what you like and don’t like.

BECOME THE BEST LOVER EVER
This is very easy if you follow one simple guideline: No one comes until she comes. Your rocks are easy to get off. Focus on her pleasure. If you want to be a memorable lover, learn not to be a selfish lover. I’m shocked when I hear stories from women about men they’ve slept with with multiple times and still haven’t concerned themselves with giving her an orgasm. I’m like, “Is this guy 19?!?” Maybe some men don’t realize this because we are wired very differently, but unlike with men, an orgasm doesn’t trigger an immediate desire to nap. A female orgasm just triggers the desire to have four more orgasms.

BE A STAND-UP GUY
I’m going to go into this in greater detail in a later column, because it deserves its own, but here are the basics: If you say you’re going to do something, do it. Offer to help your buddy move. Pick up/drop off family at the airport. Volunteer once in a while. I assume you already are, because Playboy readers tend to be men of depth and culture, but be a gentleman. Open doors. Keep your lady on the inside of the sidewalk. This stuff is so rare these days, it will make you stand out, and it goes a long, long way to signaling what kind of man you are.

USE PROTECTION
I had an ex who couldn’t get over the fact that he got a woman pregnant and she had the kid. I’m like, “Um, you could have used a condom.” It wasn’t like she tricked him. He wasted years blaming her for ruining his life instead of just owning up to his part. (The irony is, he’s a great fucking dad, and it’s made him a much better person, but they’re not all happy endings like that.) Everything happens for a reason, and YOU’RE USUALLY THE REASON. You don’t want a kid yet? Take responsibility for your side of the birth control.

DON’T WASTE TIME SETTLING
I’ve touched on this a lot, but I’m going to remind you again. In general, wasting time in life is a bad idea. A few of my only regrets are waiting tables and sitting at a bar drinking away precious years in my 20s, thinking my life was over. IT’S NOT. Cut out dead-end jobs and dead-end relationships. You won’t get the chance to be this young and this free ever again.

LEARN HOW TO BE ALONE
All the greats knew the importance of solitude. Get comfortable in your own skin.

YOU CAN ONLY WIN
If I learned anything from my 20s it’s that whatever choice you make can still be exactly the right choice. Now you might be saying, “Well why the fuck did I even read this, Bridget?” Because there are many paths, and the best one isn’t necessarily the one your parents or someone on the internet tells you to take, but YOUR OWN. Your 20s are about finding that path. And if you’re reading this and you’re already over 20, take it from me: It’s never too late.